Hydrochloric Acid → Phenyl(1-hexynyl)isopropoxyborane

HRID 1608077Notes

Reaction equation

HRID 1608077 reaction equation
[C:1]([Li])#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].C#CCCCC.C([Li])CCC.[C:19]1([B:25](OC(C)C)[O:26][CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.C=C(C)C>C(OCC)C>[C:6]1([B:25]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:26][CH:27]([CH3:28])[CH3:29])[CH:5]=[CH:4][CH:3]=[CH:2][CH:1]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8255IsobutyleneHCID 127321-HexyneHCID 569210Bis(1-methylethyl) B-phenylboronateHCID 178418339ButyllithiumHCID 178506798HCID 178506798, compound

Product 1

HCID 13721780Phenyl(1-hexynyl)isopropoxyborane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

The title compound was prepared following the method of Example 14, using 1-hexynyllithium (64 mmol) prepared from 1-hexyne and n-butyl lithium in ethyl ether (64 mL) and phenyldiisopropoxyborane (11.96 g, 58 mmol) dissolved in ethyl ether (60 mL) and quenched with hydrogen chloride in ethyl ether (18.7 mL, 64 mmol). Yield. 11.2 g (86%), bp 102°-105° C. (0.4 mm Hg); n20D 1.5008; proton NMR (CDCl3)δ7.90 (m, 2H), 7.31 (m, 3H), 4.87 (septet, J=18 Hz, 1H), 2.33 (triplet, J=18 Hz, 2H), 1.23 (d, J=18 Hz, 6H), 0.90 (triplet, 3H); boro NMR (CDCl3)δ+36.5 ppm(s); mass spectrum (chemical ionization, isobutene) m/e 229 (M+H, 10%); IR (thin film) 2195, 1324 cm-1. Anal. Calcd. for C15H 21 BO: C, 78.97; H, 9.28. Found: C, 78.18; H, 9.27.

Workup

  1. customYield

Sources & evidence

ORD record
ord-16abfdfd42b6452c9b4422c19a3f61aa
Source dataset
uspto-grants-1989_09
Patent number
US04868337

Reaction notes

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